(Z)-4-Oxo-2-pentenoic acid methyl ester

Base Information

• Chemical Name: (Z)-4-Oxo-2-pentenoic acid methyl ester
• CAS No.: 19522-27-1
• Molecular Formula: C6H8O3
• Molecular Weight: 128.12600
• Mol file: 19522-27-1.mol

Synonyms:4-oxo-pent-2c-enoic acid methyl ester;cis-β-Acetyl-acrylsaeuremethylester;4-Oxo-pent-2c-ensaeure-methylester;cis-Methyl-4-oxo-2-pentenoat;(Z)-4-Oxo-pent-2-enoic acid methyl ester;

Chemical Property of (Z)-4-Oxo-2-pentenoic acid methyl ester

Chemical Property:

• Boiling Point: 62 °C (0.2 mmHg)
• PSA: 43.37000
• LogP: 0.30460

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-4-Oxo-2-pentenoic acid methyl ester

There total 7 articles about (Z)-4-Oxo-2-pentenoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

2-methoxy-5-methyl furan (37104-34-0) → Methyl (Z)-4-oxo-2-pentenoate (19522-27-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1055/s-1984-30812

Reference yield: 56.0%

methyl (E)-4-oxo-2-pentenoate (2833-24-1) → Methyl (Z)-4-oxo-2-pentenoate (19522-27-1)

Guidance literature:

In ethanol; at 25 ℃; for 8h; Irradiation;

DOI:10.1021/jo952284p

Reference yield:

2,5-dihydro-2,5-dimethoxy-2-methylfuran (22414-24-0) → Methyl (Z)-4-oxo-2-pentenoate (19522-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / conc. H₂SO₄ / various solvent(s) / 250 °C

2: 70 percent / pyridinium chlorochromate / CH₂Cl₂ / 0.17 h / Ambient temperature

With sulfuric acid; pyridinium chlorochromate; In dichloromethane;

DOI:10.1055/s-1984-30812

upstream raw materials:

4-oxopent-2-ynoic acid methyl ester

(E)-1,1-dichloro-4-methoxy-pent-3-en-2-one

sodium methylate

2-methoxy-5-methyl furan